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<h1><a href="https://archiveofourown.org/works/26532652">Five Times Jay Tried To Propose (and One Time They Both Did)</a> by <a class='authorlink' href='https://archiveofourown.org/users/BuckyAndDanno/pseuds/BuckyAndDanno'>BuckyAndDanno</a></h1>

<table class="full">

<tr><td><b>Series:</b></td><td>Evan Buckley/Jay Halstead Fics [2]</td></tr>

<tr><td><b>Category:</b></td><td>9-1-1 (TV), Chicago PD (TV)</td></tr>

<tr><td><b>Genre:</b></td><td>5+1 Things, Evan Buckley-Severide, Fluff, Humor, M/M, Sweetness, Team Bay, proposal</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-09-18</td></tr>

<tr><td><b>Updated:</b></td><td>2020-09-18</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-06 05:54:07</td></tr>

<tr><td><b>Rating:</b></td><td>Teen And Up Audiences</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>1,905</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/26532652</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/BuckyAndDanno/pseuds/BuckyAndDanno</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>What it says on the tin. Jay tries to propose; every time something goes hilariously wrong. Then one time, Evan has the same idea.</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Evan "Buck" Buckley/Jay Halstead</td></tr>

<tr><td><b>Series:</b></td><td>Evan Buckley/Jay Halstead Fics [2]</td></tr>

<tr><td><b>Series URL:</b></td><td>https://archiveofourown.org/series/1929322</td></tr>

<tr><td><b>Comments:</b></td><td>10</td></tr>

<tr><td><b>Kudos:</b></td><td>190</td></tr>

</table>

<a name="section0001"><h2>Five Times Jay Tried To Propose (and One Time They Both Did)</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>Ya’ll have gotten me obsessed with this pairing and, since no-one else is writing it, I’m trying to make the tag stick, haha! Also I just needed some pure fluff!</p>
    </blockquote></div><div class="userstuff module">
    
    <p>Jay Halstead was in love.</p><p>Now, this was something that – years ago – he’d never thought would happen. With his job there was never time for dating, or anything serious, and in all honesty he knew he probably had a short life expectancy.</p><p>Still, he loved his job, so he didn’t mind… much.</p><p>Then he met Kelly Severide, and through him, met Evan Severide, and everything changed.</p><p>The pair had been together for a little over two years now, and Jay knew his life was brighter for having Evan in it. He knew he wanted to do everything in his power to keep Evan with him forever – to keep his better half happy and joyful and loved until the end of time.</p><p>He knew that he wanted forever with this man; wanted it all.</p><p>So Jay had, on his day off, gone to a lovely little ring store in town and picked out the perfect one for Evan.</p><p>He was going to propose.</p><p>He just needed Kelly’s blessing first.</p><p>Station 51 was quiet that afternoon, so Jay sidles into the truck bay and starts looking carefully around for the elder Severide. He knows Evan is working too, so he has to make this discreet.</p><p>Luckily, he finds him alone by the squad truck, sorting through equipment.</p><p>“Kelly.” He half whispers, smiling brightly.</p><p>“Jay!” Kelly seems surprised by the man’s sudden appearance, and more so by the way Jay gestures to keep his voice down, but he shrugs and embraces the man anyway. “What are you doing here?”</p><p>“I… uh… I wanted to run something by you.”</p><p>Kelly frowns, taking in the way the man is standing nervously, one hand in his pocket. “Are you serious?”</p><p>“What?”</p><p>Kelly grins. “Are you gonna make an honest man out of my little brother?”</p><p>Jay splutters, failing to hide his surprise. “How… How did you?”</p><p>Kelly’s grin widens. “I looked about the same when I was asking Matt’s dad.”</p><p>The two Lieutenants were due to be married the following February, and Jay couldn’t be happier for them.</p><p>Kelly slaps him on the shoulder, squeezing tight and says. “Welcome to the family, man.”</p><p>“I haven’t even asked yet.”</p><p>“He’ll say yes.” Kelly’s eyes drift over Jay’s shoulder as Evan emerges from the gear locker. “Call it brother’s instinct.”</p><p>Jay hopes he’s right.</p><p> </p><p>1 – The Restaurant</p><p> </p><p>It’s maybe a little cliché, but Jay knows that Evan deserves everything good in life, so if he’s gonna propose, it’s gonna be at a fancy restaurant.</p><p>He picks Evan’s favourite, and goes ahead beforehand to give them the ring and ask them to slip it into one of the champagne glasses when they’re served desert. The restaurant say they’ve done it before and had a great success rate. They wish him luck, and Jay feels pretty good about the whole thing.</p><p>Evan’s excited to go out for their anniversary, and delightedly picks his favourites from the menu. He loves the small booth Jay procured for them, along with the added candles and lake view window.</p><p>“It’s so romantic.” He swoons, half joking and half serious, as they sit down.</p><p>“Only the best for my prince.” Jay replies.</p><p>Evan grins. “Do I get a tiara?”</p><p>Jay hopes he’ll be adorned in bling soon enough.</p><p>When it’s finally time for dessert, Jay is practically vibrating in his seat, more so when Evan takes his sweet time (no pun intended) picking what he wants.</p><p>Eventually Jay just tells the waiter that they’ll have one of everything.</p><p>“Why the rush?” Evan asks with a laugh and Jay stammers out a response about having something else planned.</p><p>“Ooo I can’t wait.” Evan laughs, taking a sip of wine. Somehow it goes down the wrong way, and he starts coughing softly, trying to shift the sudden tickle in his throat. Reaching out to one of the waiters, he asks for a glass of water.</p><p>Jay wishes he could have seen it all go wrong before it happened.</p><p>The water arrives before the desserts, and Evan quickly takes a few gulps. Jay sees the flash of silver at the last minute, reaches out, shouts, but it’s gone.</p><p>There’s a moment of stillness, and then Evan’s eyes bug out, face turning red as he chokes on the obstruction.</p><p>Jay swears, slipping out of his seat and forcing Evan into the Heimlich manouver.</p><p>One. Two. Three.</p><p>The ring dislodges with a gasp from Evan, flying from his mouth. It hits someone across the room on the back of their head, before landing in a pile of mashed potato as a waiter walks passed.</p><p> </p><p>2 – Mr Tibbles</p><p> </p><p>After the restaurant fiasco, Jay decided he might be better going with a home cooked meal. This way, the ring is on his person at all times, and he can wait until the perfect moment to pop that all important question.</p><p>Unfortunately, fate – or in this instance, the cat – has other ideas.</p><p>He’s finished bringing out the food and has just sat down, when he notices Evan’s already teary. When questioned, his boyfriend just smiles and says, “We had a rough call today. It just made me appreciate everything I have with you.”</p><p>If they were in a movie, or a musical, this is where petals would start falling and music would start and everything would point Jay to the fact that this is the perfect moment. So he slips his hand into his pocket and pulls out the ring, readying himself to slide down onto one knee.</p><p>Then Mr Tibbles, their rambunctious (read: Evan’s worst nightmare) cat, decides to leap onto the table. Somehow this causes the already wobbly leg to snap, sending the table crashing down in front of Evan and causing all the food to slide off onto his lap.</p><p>Evan jumps up, cursing as his pants are covered in hot gravy.</p><p>In all the sudden commotion, Jay jerks and drops the ring, which Mr Tibbles proceeds to then bat under the couch.</p><p>Still muttering curses, Evan says, “I’m gonna grab a shower.”</p><p>Jay sighs and replies. “Shall we order pizza?”</p><p> </p><p>3 – The Fairground</p><p> </p><p>In all honesty he’d had a much better plan for this one. He was simply going to ask the operator of the ferris wheel to stop them at the top, and that would be it.</p><p>Unless an angry swarm of seagulls attacked them, he doubted anything could go wrong.</p><p>Evan first wanted to ride the rollercoaster though, and Jay had never been able to deny him anything. What they hadn’t expected was for the ride to halt as they reached one of the summits. Still, they were fairly level, and so Jay thought it would make an interesting story to tell the grandkids one day.</p><p>Evan, clearly, did not have the same impression.</p><p>“I read that from 1987 to 2000, there were an estimated 4.5 deaths per year on fairground rides. It doesn’t seem that much but it still makes you wonder…”</p><p>“Evan?” Jay tries to garner his boyfriend’s attention, ring held in his hand, ready to go.</p><p>Evan will not however be deterred. “I suppose you could say anything is dangerous though. Crossing the road. Eating. I mean, I still don’t know what it was I choked on when we went to La Roche last month.”</p><p>“Evan?”</p><p>The ride lurches suddenly, sending them plummeting down the slope. Jay can feel the moment the ring slips from his grasp, while Evan simply screams with exhilaration.</p><p>When they reach the end, slipping from their car, Evan says, “were you gonna say something?”</p><p>Jay just sighs and tells him he’ll be right back, then heads over to the operator to ask about retrieving the ring.</p><p>Fourth time’s the charm, right?</p><p> </p><p>4 – Wallpaper</p><p> </p><p>Jay really <strong>really </strong>doesn’t understand how this one went wrong.</p><p>They’re in the spare room, which Evan is busy wallpapering for Shay’s new baby.</p><p>“My godson is gonna need a room when he comes to stay with his favourite uncle, you know?” Evan had said when Jay had asked why he had decided to spend money on the $200 worth of baby equipment that had suddenly arrived one Saturday.</p><p>The room is mostly bare, except for a few old sheets, the wallpaper, and the tub of paste. It’s practically accident proof.</p><p>Jay slips the ring from his pocket once more. “Evan?”</p><p>He’s just about to go down on one knee when Evan turns, roll of wallpaper hoisted on one shoulder. He turns so quickly that the end of the roll hits the side of Jay’s head before the other man can move, knocking him to the floor.</p><p>He’s disorientated for a long moment, Evan knelt quickly at his side with an apology and asking if he’s okay, before he realises that he’s no longer holding the ring.</p><p>Scrabbling over to where he was stood, he just about sees it sink into the paste, and then it’s gone.</p><p> </p><p>5 – The Storm</p><p> </p><p>Movie night.</p><p>Nothing at all can go wrong.</p><p>The cat’s in the bedroom.</p><p>There are no candles, glassware or other dangerous objects around.</p><p>They’re stationary.</p><p>There’s no rolls of wallpaper.</p><p>No food to be choked on.</p><p>Simply them and a couch and a blanket and the TV.</p><p>Foolproof. Literally. <strong>Fool</strong> proof.</p><p>“Evan?”</p><p>His boyfriend turns to him with a smile, snuggling closer. “Yeah Jay?”</p><p>“I – ”</p><p>He doesn’t get any further before the room is plunged into darkness.</p><p>Outside, he can definitely hear the distinct sound of a rather vicious storm.</p><p>“Power’s out.” Evan chuckles. “Looks like the landlord hasn’t fixed the breaker yet after the last storm.”</p><p>Jay sighs. “I’ll get the torch.”</p><p> </p><p>6 – The Double Yes</p><p> </p><p>The next day, he actually pays the landlord to fix the breaker.</p><p>He orders pizza.</p><p>He waits for Evan to come home.</p><p>This is it. This is the day.</p><p>He’s not going to let anything ruin it now.</p><p>When Evan arrives home, he settles his boyfriend down at the table, flicks on the electric candles (safety first) and then;</p><p>“Evan, from the moment I met you, I knew you were the one for me. I can’t imagine spending any day of my life without you, and I…” He trails off as he pats his pocket; suddenly realises that in all his preparedness to not screw this one up – ie, not carrying the ring until he actually needed it – that he’d yet to actually get it from the dresser in their room.</p><p>“Um… one moment…”</p><p>So much for not screwing it up.</p><p>Diving into the sock drawer, he procures the box with little hassle, slipping the ring from its casing and then turning back to the door.</p><p>Silhouetted in the frame, Evan is down on one knee, his own ring outstretched.</p><p>Jay’s jaw drops.</p><p>Evan grins. “I got the feeling you were trying to ask me something, but you liked to take your sweet time.”</p><p>“I wanted it to be perfect.” Jay whispers.</p><p>“Every minute with you is perfect.”</p><p>Jay practically melts where he’s stood.</p><p>“Well?” Evan is still grinning. “Together?”</p><p>Jay chuckles and walks over to his boyfriend, sinking down onto one knee opposite him. “Evan?”</p><p>“Jay?”</p><p>“Will you marry me?” Their voices speak in unison, joint grins on each of their faces. “Yes.”</p><p>A kiss punctuates the moment, and when they break away, Jay can’t help but laugh. “Well this is definitely one to tell the grandkids.”</p><p>Evan just kisses him again. “One thing at a time, babe.”</p><p>“You got it, tiger.”</p>
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